SYNTHESIS OF (2S,3R,7RS)-STEGOBINONE (2,3-DIHYDRO-2,3,5-TRIMETHYL-6-(1-METHYL-2-OXOBUTYL)-4H-PYRAN-4-ONE) AND ITS (2R,3S,7RS)-ISOMER. THE PHEROMONE OF THE DRUGSTORE BEETLE

Article abstract of DOI:10.1016/S0040-4020(01)97687-2

Reaction of acetaldehyde with the trianion of 4,6-dimethylnonane-3,5,7-trione followed by acidification yielded a stereoisomeric mixture of stegobinone, the pheromone of Stegobium paniceum L.Acylation of the dianion derived from 4-methylheptane-3,5-dione